From CLI, browse into the directory containing the gpg.exe file (For me, it's C:\Program Files\GPG\). Similarly, generate a key with:
gpg --gen-key
I'm now going to make one for my Hotmail account, which is syraxius@hotmail.com. Now, export your public key from Linux and mail it to your Hotmail account. To export the keys, type:
gpg --export kelvin@syraxius.ath.cx > public.key
Now send it to your guy in Windows through FTP (remember to set it to binary) or any other means. Now your public.key should be in the same folder as your gpg.exe. Type this to import the key:
gpg --import *.key
Now you should be able to encrypt files that are only readable by kelvin@syraxius.ath.cx. I'm going to type a message and echo it into encrypt like this:
echo Hello this is a test message! | gpg --encrypt -r kelvin@syraxius.ath.cx -a > message.asc
Now you should have a message.asc. Open it with notepad and paste it into Hotmail, just make sure that you have Plain Text as the text mode. Once you receive the mail, Alpine should prompt for your private key password, and the message would be decrypted.
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